Production method for cyclopentanone derivative, intermediate compound, and production method for intermediate compound

Abstract

The present invention is a production method for a compound represented by the following general formula (V), the method comprising a step of obtaining a compound represented by the following general formula (II) by reacting a compound represented by the following general formula (I) with an acid: wherein, G 1 and G 2 are each a protecting group that dissociates under acidic conditions.

The invention claimed is: 
     
       1. A production method for a compound represented by formula (III), comprising:
 obtaining a compound represented by formula (III) below by reacting a compound represented by formula (II) with a compound selected from the group consisting of a formaldehyde, paraformaldehyde, 1,3,5-trioxane, and formaldehyde dialkyl acetal: 
 
       
         
           
           
               
               
           
         
       
       in formula (II), X is a halogen atom, an alkyl group having from 1 to 4 carbons, a haloalkyl group having from 1 to 4 carbons, an alkoxy group having from 1 to 4 carbons, a haloalkoxy group having from 1 to 4 carbons, a phenyl group, a cyano group, or a nitro group; m is an integer from 0 to 5; a plurality of X moieties may be the same or different when m is 2 or greater; and 
       
         
           
           
               
               
           
         
       
       in formula (III), X and m are each the same as X and m in formula (II). 
     
     
       2. A production method for a compound represented by formula (IV), comprising:
 obtaining a compound represented by formula (IV) below by reacting a compound represented by formula (III) with protecting groups that dissociate under acidic conditions: 
 
       
         
           
           
               
               
           
         
       
       in formula (III), X is a halogen atom, an alkyl group having from 1 to 4 carbons, a haloalkyl group having from 1 to 4 carbons, an alkoxy group having from 1 to 4 carbons, a haloalkoxy group having from 1 to 4 carbons, a phenyl group, a cyano group, or a nitro group; m is an integer from 0 to 5; a plurality of X moieties may be the same or different when m is 2 or greater; and 
       
         
           
           
               
               
           
         
       
       in formula (IV), X and m are each the same as X and m in formula (III); and G 1  and G 2  each represents a protecting group that dissociates under acidic conditions, G 1  and G 2  may be the same or different, and G 1  and G 2  may bond with one another to form a ring. 
     
     
       3. A production method for a cyclopentanone derivative represented by formula (V), comprising:
 obtaining a compound represented by formula (V) by dehydroxymethylating a compound represented by formula (IV) under basic conditions: 
 
       
         
           
           
               
               
           
         
       
       in formula (V), X is a halogen atom, an alkyl group having from 1 to 4 carbons, a haloalkyl group having from 1 to 4 carbons, an alkoxy group having from 1 to 4 carbons, a haloalkoxy group having from 1 to 4 carbons, a phenyl group, a cyano group, or a nitro group; m is an integer from 0 to 5; a plurality of X moieties may be the same or different when m is 2 or greater; G 1  and G 2  each represents a protecting group that dissociates under acidic conditions, G 1  and G 2  may be the same or different, and G 1  and G 2  may bond with one another to form a ring; and 
       
         
           
           
               
               
           
         
         in formula (IV), X, m, G 1 , and G 2  are each the same as X, m, G 1 , and G 2  in formula (V). 
       
     
     
       4. The production method for a cyclopentanone derivative according to  claim 3 , wherein the compound represented by formula (V) is a compound represented by formula (Va) below: 
       
         
           
           
               
               
           
         
       
       in formula (Va), X and m are each the same as X and m in formula (V); Y 1  and Y 2  are each independently a hydrogen atom, an alkyl group having from 1 to 4 carbons, an alkenyl group having from 1 to 4 carbons, or a substituted or unsubstituted phenyl group, naphthyl group, or benzyl group; and Y 1  and Y 2  may bond with one another to form a ring. 
     
     
       5. The production method for a cyclopentanone derivative according to  claim 4 , wherein Y 1  and Y 2  are each independently a hydrogen atom or an alkyl group having from 1 to 4 carbons. 
     
     
       6. The production method for a cyclopentanone derivative according to  claim 1 , wherein both Y 1  and Y 2  are methyl groups. 
     
     
       7. The production method for a cyclopentanone derivative according to  claim 3 , wherein the compound represented by formula (V) is a compound represented by formula (Vb) below: 
       
         
           
           
               
               
           
         
       
       in formula (Vb), X and m are each the same as X and m in formula (V); and G 1b  and G 2b  are each independently an alkoxymethyl group having from 1 to 4 carbons in an alkoxy moiety, an alkoxyethyl group having from 1 to 4 carbons in an alkoxy moiety, an alkyl group having from 1 to 4 carbons, an allyl group, or a substituted or unsubstituted benzyl group, tetrahydropyranyl group, or tetrahydrofuranyl group. 
     
     
       8. The production method for a cyclopentanone derivative according to  claim 3 , wherein in formula (V), m is an integer from 0 to 3, and when m is 1 or greater, X is a halogen atom, an alkyl group having from 1 to 3 carbons, a haloalkyl group having from 1 to 3 carbons, an alkoxy group having from 1 to 3 carbons, or a haloalkoxy group having from 1 to 3 carbons. 
     
     
       9. The production method for a cyclopentanone derivative according to  claim 3 , wherein in formula (V), m is an integer from 0 to 2, and when m is 1 or 2, X is a halogen atom.